Delegation In Business Will Break Your Heart – Do It Anyway

Picture this:

You’re a passionate entrepreneur, knee-deep in the trenches of your startup.

You wear all the hats, from coding to marketing, because nobody does it quite like you, right?

Fueled by late nights and strong coffee, you have less and less time to grow the business, and thoughts about delegation keep popping up in your mind:

“Should someone else be doing some of these tasks instead of me? But who? Who would be able to do it as well as I do? My clients and customers will definitely feel the difference. What do I do?”

And you just can’t figure out the answer. Trust me, I know the feeling.

This uncertainty is actually really common.

I have to be honest with you, though – my friend, you are the bottleneck to your own growth.

‘Cause if you can’t take this leap and go from technician to CEO… you’ll never grow past yourself.

In this article, I’ll show exactly why trusting others and delegating is SO damn hard, how to find the courage to let go, and most importantly…

… how to actually go about delegation in business without breaking the entire business you put your heart and soul into.

I hate when gurus say “build systems and processes, delegate, blah blah blah…” but never actually show how to do it. It always sounds so abstract.

Not here.

Why Delegation Is So Psychologically Difficult: It Starts With Your Identity

Look man, I get it.

You built this thing. The last thing you would want is to hire some guy who takes the quality down a notch and makes it feel bland.

And you don’t just love the end result, you love the doing.

I mean, you might have spent years building up the necessary skills to perform your tasks so well. These tasks are literally part of who you are.

And giving them up might feel like giving up who you are.

Letting go of tasks you built, care about, or love doing feels like betrayal — to yourself, your standards, and sometimes your team.

This is why you probably can’t decide whether to delegate or not. I don’t think you’ll be able to decide on your behavior before you decide on your identity.

Are you a technician, or are you a CEO? That’s the question.

If you know you want to actually be a CEO and scale your company into the millions, then you’ll have to switch your current identity.

But if you decide you’d rather do all the tasks forever, that’s fine as well. But then you’re not running a business, you’re merely self-employed. More on that later.

The Chaos Phase: Delegation In Business Gets Worse Before It Gets Better

I’m not going to BS you and tell you that all your fears are irrational and that your employees won’t bring the quality of your products or services down.

Yeah, they will. They’ll make mistakes, and you’ll think, “What the hell am I doing?”

You’ll be appalled by how much people can misunderstand you and by how many deadlines can be missed.

But you have to understand (and every successful founder does) that…

People need time. They need to fail and then calibrate.

You have to trust them through this moment of “ew, what the hell did they just make, how will they ever do it like I do it?!”

Don’t judge and be patient. Once they do learn (and if you made a good hire, they will), it’s just an upside from there.

So, take a deep breath and learn to let go. If you step in every time, they’ll never learn — and you’ll never scale.

There are two “types” of effective delegation:

• With a clear and detailed set of instructions: This works well in large, bureaucratic organizations where tasks are standardized, and employees can be lower-level, as they follow the precise instructions given. Or for very low-level tasks like the ones you give to your virtual assistant.
• True delegation: Here, you assign a goal or outcome rather than specific instructions. You focus on the result and allow the person to decide how to achieve it, accepting that they may approach the task differently from how you would. This requires patience and tolerance for different methods and a willingness to let go of micromanagement.

The last point I want to make for this section is that your presence in every process feels helpful, but it kills momentum.

You can’t think strategically when your mind is drowning in tactical noise. You’re supposed to think more and do less if you want to scale.

You’re very smart, alright? Use it.

And since I believe you’re smart, I’ll offer you an extremely helpful resource I made to help you make the difficult decisions in your startup.

You’ll get the basics of everything you need to know to launch a successful startup, from idea to marketing, to finance, to decision-making, etc.

It’s my 8D framework for launching your business, and it’s completely free. All you have to do is click this beautiful button:

How to Delegate Without Breaking The Whole Damn Business

Since delegation can be so scary, why not make it incremental?

You don’t have to give someone 100% responsibility over a part of your business tomorrow.

I recommend you start small and THEN expand.

That way, your employees can take it step by step and gradually take on more responsibility, so you’re both sure no one clicks the “NUKE BUSINESS” button.

So delegate small tasks first, then graduate to higher-impact ones.

Tell them: “Today you do one thing… then gradually move up the chain, higher, higher, and higher.”

They’ll have more time to observe and learn, and you’ll actually be able to sleep at night.

And when you do eventually give them some more responsibility…

… Back the hell off.

Undermining their calls kills morale and creativity. When they have more autonomy (that they have earned), trust me, they’ll do their best work for you.

Leadership psychology has shown this time and time again – the more respected and autonomous an employee feels, the better their output.

You want good output, right?

Another important consideration you want to make when hiring is:

“Are they a creator or just an executor?”

I always tried to hire people who have an internal need to create. Those who want to create things individually, without being told what to do all of the time.

Not performers, but precisely those who will themselves move something forward, who are themselves interested in doing something.

I was listening to a podcast from the legend Alex Hormozi, and I remember him saying:

“Hiring talented people is one of the easiest 10x-100x ROI opportunities. And there’s always underpriced talent.”

Creators are those who will get you that ROI.

The Courage To Let Go (Even When It’s Not Perfect)

Once again, effective delegation requires emotional maturity. It’s just like any other human relationship.

You’ll feel disappointment, frustration, fear even.

But if you want to scale, I invite you to do it anyway. Trusting is a muscle you build, not a switch you flip.

It takes time and experience to get less emotionally impacted by stressful work situations.

Less-than-ideal employee performance is one of them.

Also, stop expecting to hire someone “just like you”.

That is NOT the point.

You should actually find someone who’s even better than you (at a certain task). That’s a very mature decision, as the master will be outshined.

(but who cares, as long as the master makes extra cash, am I right?)

Should I Delegate If I Love The Work? You Don’t Have To, But Be Honest.

If you truly want to stay in the work forever — great. There’s absolutely nothing wrong with it, and you can make a nice living like that.

Just stop calling it a scalable startup.

If you can’t replace yourself — you’re not running a business. You’re self-employed.

And in some cases, you’ve built yourself a prison.

So, even if you decide to take care of all of the business tasks yourself, make sure to create systems and processes for yourself.

Find ways to operationalize your tasks so they take you way less time to complete.

Specifically, find patterns in your work and build SOPs (standard operating procedures) so you don’t have to reinvent the wheel every time you close a client or create a product.

That’s how you lower your work time, increase your effective hourly rate… and best of all – if you decide to delegate one day, you can.

You already built the necessary systems.

Takeaways

In this article, I zoomed into delegation in business and looked at why it’s so painful and uncomfortable. But honestly, as soon as something is very uncomfortable, you know it’s worth doing.

In business and in life, it’s always those tasks we least want to do that will give us the best progress.

I also told you some specifics of how to actually go about delegation. Here’s a summary:

• If you can’t take the leap from technician to CEO, you’re likely a bottleneck in your business.
• You might identify with your expertise and the tasks you love doing, so giving them up feels like giving up a part of yourself. That’s why delegation is so psychologically difficult.
• You have to endure the ‘chaos phase’. As soon as you hire someone, they’ll probably make lots of mistakes. The quality won’t be as high as you’d like it to be. And that’s okay. Hiring is a long game, and it’s totally worth it.
• Don’t give people 100% responsibility straight away. Give them smaller tasks and let them graduate to the more important ones.
• When you do give someone more responsibility, back off. People need autonomy to do their best work.
• Hire creators, not mere executors. Creators are people who have lots of initiative and want to do things by themselves, without you having to explicitly tell them. They bring their own expertise and ideas, and they’re not afraid of trying out new things.
• The courage to let go is not an easy thing to have. But if you’re a mature adult, I believe in you; it’s totally doable.
• If you love your work, you don’t HAVE to delegate. But then, you’re self-employed, you’re not running a business. That’s completely fine.
• Still, make systems and processes (like SOPs) around your own work so you can spend less time working and more time thinking, growing, or living.